2-(4-hydroxyphenyl)-4,4-dimethyl-2-oxazoline | 124438-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxyphenyl)-4,4-dimethyl-2-oxazoline
• 英文别名: 4-(4,4-Dimethyl-1,3-oxazolidin-2-ylidene)cyclohexa-2,5-dien-1-one；4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)phenol
• CAS: 124438-10-4
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: ZHEBOGJEFDFDSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-4,4-dimethyl-2-oxazoline 、 1-(phenylmethyl)-4-piperidinepropanol methanesulfonate(ester) 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以13.5 parts (40.9%)的产率得到4-[3-[4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenoxy]propyl]-1-(phenylmethyl)piperidine
  参考文献：
  名称：

  Novel pyridazinamine derivatives

  摘要：

  具有抗病毒活性的新型吡啶唑胺衍生物，含有这些化合物的组合物以及用所述化合物破坏或防止病毒生长的方法，用于治疗由这些病毒引起的疾病的温血动物。以及制备所述化合物和组合物的方法。

  公开号：

  US04992433A1
• 作为产物：
  描述：

  N-(1,1-dimethyl-2-hydroxyethyl)-4-hydroxybenzamide 在 氯化亚砜 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 以8.02 g的产率得到2-(4-hydroxyphenyl)-4,4-dimethyl-2-oxazoline
  参考文献：
  名称：

  2-(4-Hydroxyphenyl)-4,4-dimethyl-2-oxazoline: X-ray and density functional theory study

  摘要：

  In the crystal structure of the title compound, C11H13NO2, there are strong intermolecular O-H center dot center dot center dot N hydrogen bonds which, together with weak intramolecular C-H center dot center dot center dot O hydrogen bonds, lead to the formation of infinite chains of molecules, held together by weak intermolecular C-H center dot center dot center dot O hydrogen bonds. A theoretical investigation of the hydrogen bonding, based on density functional theory (DFT) employing periodic boundary conditions, is in agreement with the experimental data. The cluster approach shows that the influence of the crystal field and of hydrogen-bond formation are responsible for the deformation of the 2-oxazoline ring, which is not planar and adopts a T-4(3) (T-C3(C2)) conformation.

  DOI：

  10.1107/s0108270106019238

文献信息

• Regioselective Functionalization of Ester-, Amide-, Carbonate-, and Carbamate-Substituted 2-Phenyl-2-oxazolines with Mixed Lithium–Magnesium Amides
  作者：Leandro A. Bozzini、Thiago dos Santos、Valter E. Murie、Murilo B. M. de Mello、Ricardo Vessecchi、Giuliano C. Clososki

  DOI：10.1021/acs.joc.0c02369

  日期：2021.1.1

  highly functionalized benzene derivatives by regioselective metalation of ester-, amide-, carbamate-, and carbonate-substituted 2-phenyl-2-oxazolines with mixed lithium–magnesium amides followed by reaction with different electrophiles. While a complementary metalation site can be accessed by using different bases, steric and electronic effects promoted by the aromatic ring substituents also play an important

  我们通过将酯，酰胺，氨基甲酸酯和碳酸盐取代的2-苯基-2-恶唑啉与锂-镁酰胺混合体进行区域选择性金属化，然后与不同的亲电试剂反应，制备了新型的高度官能化的苯衍生物。尽管可以通过使用不同的碱基来访问互补的金属化位点，但由芳环取代基促进的空间和电子效应在反应区域选择性中也起着重要作用。芳香族氢p K a值的计算计算已帮助我们通过络合物诱导的邻近效应概念使金属化偏好合理化。
• Generation and Suppression of 3-/4-Functionalized Benzynes Using Zinc Ate Base (TMP−Zn−ate):  New Approaches to Multisubstituted Benzenes
  作者：Masanobu Uchiyama、Yuri Kobayashi、Taniyuki Furuyama、Shinji Nakamura、Yumiko Kajihara、Tomoko Miyoshi、Takao Sakamoto、Yoshinori Kondo、Keiji Morokuma

  DOI：10.1021/ja071268u

  日期：2008.1.1

  6-tetramethylpiperidino)zincate (R2Zn(TMP)Li) through deprotonative zincation as a key reaction. In this system, by choosing appropriate ligands for the zincate, either regioselective zincation of functionalized haloaromatics or the generation of substituted benzynes can be controlled in good yields with excellent chemoselectivity, using the same substrate. Zincation with (t)Bu2Zn(TMP)Li followed by electrophilic

  我们详细介绍了我们通过去质子锌化作为关键反应，用二烷基（2,2,6,6-四甲基哌啶基）锌酸锂（R2Zn（TMP）Li）制备功能化苄的新方法的全部细节。在该系统中，通过为锌酸盐选择合适的配体，可以使用相同的底物以良好的产率和优异的化学选择性控制官能化卤代芳烃的区域选择性锌化或取代苄的生成。用 (t)Bu2Zn(TMP)Li 进行锌化，然后进行亲电捕获或用 Me2Zn(TMP)Li 进行锌化，然后进行亲核或二烯捕获，这被证明是化学选择性制备 1,2,3-/1,2 的有力工具,4-三取代苯衍生物。这些方法比以前合成多功能苯的方法具有更大的通用性。这种独特的苄形成反应机理的计算/理论研究表明，锌酸盐的二烷基锌部分与卤素的优先配位是消除活化能降低的原因，即形成苄的原因。还讨论了 Zn 上的配体在加速/减速消除中的作用。
• Compounds Comprising an Oxazoline or Thiazoline Moiety, Processes for Making Them, and Their Uses
  申请人：Leurs Regorius

  公开号：US20080161331A1

  公开（公告）日：2008-07-03

  The present invention relates to compounds comprising an oxazoline or thiazoline moiety, processes for preparing them, pharmaceutical compositions comprising said compounds and their uses as H 3 -receptor ligands, (I), wherein A 1 is CH C(CH 3 ) or N; R 1 is hydrogen or halogen; R 2 is (II); A 2 is O or S; R 3 is hydrogen, halogen, C 1-4 alkyl or C 1-4 alkoxy; R 4 is hydrogen, halogen, C 1-4 alkyl, C 1-4 alkoxy, trifluoromethyl or —O—(CH 2 )n-NR 12a R each CH 2 in —O—(CH 2 )n-NR 12a R 12b being optionally substituted by one or two C 1-4 alkyl; R 5 is hydrogen or —O—(CH 2 ) m —NR 13a R 13b , each CH 2 in —O—(CH 2 ) m —NR 13a R 13b being optionally substituted by one or two C 1-4 alkyl, and at least one of R 4 and R 5 should be a —O—(CH 2 )n-NR 12/13a R 12/13b group.

  本发明涉及包含氧唑啉或噻唑啉基团的化合物，制备它们的方法，包含所述化合物的制药组合物以及它们作为H3受体配体的用途，其中A1为CH、C(CH3)或N；R1为氢或卤素；R2为(II)；A2为O或S；R3为氢、卤素、C1-4烷基或C1-4烷氧基；R4为氢、卤素、C1-4烷基、C1-4烷氧基、三氟甲基或-O-(CH2)n-NR12aR12b，其中-O-( )n-NR12aR12b可以选择地被一个或两个C1-4烷基取代；R5为氢或-O-( )m-NR13aR13b，每个-O-( )m-NR13aR13b中的 可以选择地被一个或两个C1-4烷基取代，并且R4和R5中至少有一个应为-O-( )n-NR12/13aR12/13b基团。
• Compounds comprising an oxazoline or thiazoline moiety, processes for making them, and their uses
  申请人：UCB Pharma, S.A.

  公开号：US07863450B2

  公开（公告）日：2011-01-04

  The present invention relates to compounds comprising an oxazoline or thiazoline moiety, processes for preparing them, pharmaceutical compositions comprising said compounds and their uses as H3-receptor ligands, (I), wherein A1 is CH C(CH3) or N; R1 is hydrogen or halogen; R2 is (II); A2 is O or S; R3 is hydrogen, halogen, C1-4 alkyl or C1-4 alkoxy; R4 is hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, trifluoromethyl or —O—(CH2)n-NR12aR each CH2 in —O—(CH2)n-NR12aR12b being optionally substituted by one or two C1-4 alkyl; R5 is hydrogen or —O—(CH2)m—NR13aR13b, each CH2 in —O—(CH2)m—NR13aR13b being optionally substituted by one or two C1-4 alkyl, and at least one of R4 and R5 should be a —O—(CH2)n-NR12/13aR12/13b group.

  本发明涉及具有氧唑啉或噻唑啉基团的化合物，制备它们的方法，包含所述化合物的制药组合物以及其作为H3受体配体的用途，其中A1是CH、C(CH3)或N；R1是氢或卤素；R2是(II)；A2是O或S；R3是氢、卤素、C1-4烷基或C1-4烷氧基；R4是氢、卤素、C1-4烷基、C1-4烷氧基、三氟甲基或—O—(CH2)n-NR12aR，其中—O—( )n-NR12aR12b中的每个 可以选择性地由一个或两个C1-4烷基取代；R5是氢或—O—( )m—NR13aR13b，其中—O—( )m—NR13aR13b中的每个 可以选择性地由一个或两个C1-4烷基取代，且R4和R5中至少有一个应为—O—( )n-NR12/13aR12/13b基团。
• HALOALLYLAMINE INHIBITORS OF SSAO/VAP-1 AND USES THEREFOR
  申请人：McDonald Ian A.

  公开号：US20100298330A1

  公开（公告）日：2010-11-25

  The present invention is related to the preparation and pharmaceutical In use of novel haloallylamine derivatives as SSAO/VAP-1 inhibitors having the structure of Formula I, as defined in the specification:(I). The invention also relates to methods of using invention compounds, or pharmaceutically acceptable salt or derivatives thereof, for the treatment of a variety of indications, e.g., inflammatory diseases.

  本发明涉及一种具有I式结构的新型卤代烯丙胺衍生物的制备和药物应用，所述衍生物可作为SSAO/VAP-1抑制剂，I式结构如规范中定义。本发明还涉及使用本发明化合物或其药学上可接受的盐或衍生物的方法，用于治疗多种适应症，例如炎症性疾病。